Any of the simple sugars that serve as building blocks for carbohydrates. They are classified based on their backbone of carbon (C) atoms: Trioses have three carbon atoms, tetroses four, pentoses five, hexoses six, and heptoses seven. The carbon atoms are bonded to hydrogen atoms (singlehorzbondH), hydroxyl groups (singlehorzbondOH; see functional group), and carbonyl groups (singlehorzbondCdoublehorzbondO), whose combinations, order, and configurations allow a large number of stereoisomers (see isomer) to exist. Pentoses include xylose, found in woody materials; arabinose, found in gums from conifers; ribose, a component of RNA and several vitamins; and deoxyribose, a component of DNA. Important hexoses include glucose, galactose, and fructose. Monosaccharides combine with each other and other groups to form a variety of disaccharides, polysaccharides, and other carbohydrates.
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With few exceptions (e.g., deoxyribose), monosaccharides have the chemical formula Cx(H2O)y with the chemical structure H(CHOH)nC=O(CHOH)mH. If n or m is zero, it is an aldehyde and is termed an aldose, otherwise it is a ketone and is termed a ketose. Monosaccharides contain either a ketone or aldehyde functional group, and hydroxyl groups on most or all of the non-carbonyl carbon atoms.
A common way of representing the cyclic structure of monosaccharides is the Haworth projection. In Haworth projection, the α-isomer has the OH- of the anomeric carbon under the ring structure, and the β-isomer, has the OH- of the anomeric carbon on top of the ring structure. In chair conformation, the α-isomer has the OH- of the anomeric carbon in an axial position, whereas the β-isomer has the OH- of the anomeric carbon in equatorial position.
Monosaccharides are classified according to their molecular configuration at the chiral carbon furthest removed from the aldehyde or ketone group. The chirality at this carbon is compared to the chirality of carbon 2 on glyceraldehyde. If it is equivalent to D-glyceraldehyde's C2, the sugar is D; if it is equivalent to L-glyceraldehyde's C2, the sugar is L. Due to the chirality of the sugar molecules, an aqueous solution of a D or L saccharides will rotate light. D-glyceraldehyde causes polarized light to rotate clockwise (dextrorotary); L-glyceraldehyde causes polarized light to rotate counterclockwise (levorotary). Unlike glyceraldehyde, D/L designation on more complex sugars is not associated with their direction of light rotation. Since more complex sugars contain multiple chiral carbons, the direction of light rotation cannot be predicted by the chirality of the carbon that defines D/L nomenclature.
All these classifications can be combined, resulting in names like D-aldohexose or ketotriose.